63317-99-7

Usage

InChI:InChI=1/C16H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8,11-12H,2-6,9-10,13-15H2,1H3,(H,17,18)/b8-7+,12-11+

Upstream product

• 68820-32-6 (Z)-4-undecenal 
• 17857-14-6 (3-carboxypropyl)(triphenyl)phosphonium bromide 
• 1448312-51-3 2-(hexadeca-5Z,9Z-dien-1-yloxy)tetrahydro-2H-pyrane 
• 22433-33-6 Nona-1,2-dien 
• 910095-87-3 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran 
• 628-16-0 hexa-1,5-diyne 
• 91647-85-7 1,5-dodecadiyne 
• 475207-22-8 5,9-hexadecadiynoic acid 
• 250786-06-2 2-(3-undecynyl)-1,3-dioxolane 
• 250786-07-3 (Z)-2-(dec-3-en-1-yl)-1,3-dioxolane 
• 629-05-0 n-octyne 
• 475207-21-7 1-(tert-butyldimethylsilyloxy)-5,9-hexadecadiyne 
• 475207-24-0 5,9-hexadecadiynal 
• 475207-23-9 5,9-hexadecadiyn-1-ol 

Relevant academic research and scientific papers

Total synthesis and biological evaluation of (5Z,9Z)-5,9-hexadecadienoic acid, an inhibitor of human topoisomerase I

The naturally occurring (5Z,9Z)-5,9-hexadecadienoic acid was synthesized stereochemically pure in six steps starting with commercially available 1,5-hexadiyne. The title compound was antimicrobial against the Gram-positive bacteria Staphylococcus aureus (MIC 80 μM) and Streptococcus faecalis (MIC 200 μM), but inactive against Gram-negative bacteria such as Pseudomonas aeruginosa. In addition, the (5Z,9Z)-5,9-hexadecadienoic acid completely inhibits human topoisomerase I at a concentration of 800 μM, while 5,9-hexadecadiynoic acid and hexadecanoic acid do not inhibit topoisomerase I (>1000 μM). This comparison reveals that the cis double bond geometry in the title compound is required for topoisomerase I inhibition. Moreover, these results suggest that the antimicrobial activity of (5Z,9Z)-5,9-hexadecadienoic acid against either S. aureus or S. faecalis could be a result, at least in part, of the inhibitory activity of the acid against topoisomerases.

The facile synthesis of the 5Z,9Z-dienoic acids and their topoisomerase i inhibitory activity

An original, effective approach to the synthesis of natural and synthetic 5Z,9Z-dienoic acids in high yields (61-67%) and with high selectivity (>98%) was developed. The approach is based on the use of the new intermolecular catalytic cross cyclomagnesiation of terminal aliphatic and oxygenated 1,2-dienes upon treatment with Grignard reagents in the presence of the Cp 2TiCl2 catalyst. High activity of (5Z,9Z)-5,9- eicosadienoic acid as a human topoisomerase I inhibitor at concentrations above 0.1 μM was elucidated.

Facile syntheses for (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid through a common synthetic route

The Δ5,9 fatty acids (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid were synthesized for the first time in four steps (9-12% overall yield) starting from commercially available 2-(2-bromoethyl)-1,3-dioxolane. The synthetic approach provided enough material to corroborate the structure and stereochemistry of (5Z,9Z)-5,9-nonadecadienoic acid which was recently identified in the flowers of Malvaviscus arboreus (Malvaceae). The novel phospholipids 1-hexadecanoyl-2-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine and 1-octadecanoyl-2-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine were also synthesized from commercially available L-α-phosphatidylcholine (egg yolk) and characterized by positive ion electrospray mass spectrometry. These are the first examples of unsymmetrical phospholipids with saturated fatty acids at the sn-1 position and Δ5,9 fatty acids at the sn-2 position. Copyright (C) 1999 Elsevier Science Ireland Ltd.